Executive Operations assistant protecting an education and software CEO’s time through calendar, accountability, hiring, and project management. Performance-based path to Chief of Staff.
Responsibilities
Own and optimize the CEO’s calendar, protecting deep-work blocks and aligning schedules with company goals
Run internal follow-ups, action items, reminders, escalations, and communications across Slack, WhatsApp, and email
Build and manage the company operating system using Trello, Asana, Notion, or similar tools
Track project owners, deadlines, next actions, and definitions of done
Hold leaders and teams accountable for deliverables and reporting cadence
Run end-to-end hiring operations, including pipeline management, scheduling, scorecards, assignments, Loom reviews, and references
Oversee content operations for YouTube, Instagram, and email without creating content
Track weekly content output, deadlines, approvals, and delivery
Collect monthly P&L data, KPI dashboards, and weekly reports
Analyze profit and loss statements and payroll, and provide recommendations on raises, compensation structures, inefficiencies, and staffing
Execute personal and local projects supporting business performance, such as managing a home studio build-out
Advise department leaders on practical AI use in their daily responsibilities
Complete scheduling, meeting notes, and action-item tasks during onboarding
Progress from execution and systems ownership into Chief of Staff-style planning, cross-functional problem-solving, and high-priority initiative management
Requirements
Highly organized and extremely self-accountable
Strong project management skills; experience with Trello, Asana, or similar tools
Exceptional attention to detail
Strong writing and communication skills, including detailed reports and clear, direct updates
Ability to make good decisions independently and anticipate needs
Ability to hold people accountable and handle tough conversations
Discretion, trustworthiness, and comfort with high confidentiality and sensitive information
Comfort with high access and high expectations
Experience or fluency using AI tools in daily workflows; at minimum, ChatGPT instead of Google
Familiarity with Google Workspace, Slack, Trello/Asana, Calendly, Zoom, and Loom
Spanish preferred but not required
Strong overlap with EST working hours
Must complete a required 5-minute camera-on Loom video submission
Must complete the final assignment involving a Google document and embedded YouTube videos
Benefits
Performance bonus
High-speed CEO training and full context into CEO decision-making
Growth track to Chief of Staff over 12–18 months, performance-based
Remote work with strong overlap with EST working hours
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